should I apply for the stretch job or the slightly-less-of-a-stretch job?

A reader writes:

I learned through a listserv that several positions are open at a consulting firm. One is a senior level position that involves developing curricula and trainings for a variety of clients. This one made my heart race: it scares me because it would be a huge new challenge with much higher stakes, but feels more aligned with my long term career goals and really exciting. I immediately started writing a cover letter and tweaking my resume. And I wrote back to the person who posted it on the listserv and asked for a hiring manager’s name for this specific position and she nicely shared it with me. So theoretically, I could ship this application out tomorrow.

But I keep doubting my abilities to get my foot in the door, let alone succeed in the job.

This firm is also hiring a project manager. Being a project manager is not my long-term goal. But in some ways this feels like a more natural next step from what I’m currently doing, and I keep thinking that maybe I should apply for that, see if I can get an interview and get hired, and then see if it makes sense to eventually try to transition onto the trainings team.

Is this a YOLO/Lean In moment where I should apply to the harder reach of a job, or should I Lean Sideways-Diagonally-In and apply for a job that’s less exciting on paper, but would still challenge me a lot and which might be a more realistic way out of my miserable current job? I should definitely only apply to one of the two, right?

Without knowing how much of a reach the first job would be for you, it’s hard to say. If it’s one step up, absolutely you should apply. If it’s more of a stretch than that — if it would mean skipping several normal rungs on the ladder to get there — then it’s more of a question.

Do you meet most of the qualifications they listed? If so, it’s not so far out of reach that you shouldn’t apply. On the other hand, if you don’t meet many of the qualifications, then that’s an answer too.

As for whether you have to pick one and only one … I get asked versions of that all the time and wish I had a definitive answer for it, but I don’t. At some places, the best thing to do would be to apply for both. At other places, they’d really want you to pick one. And at some places, if you applied for one, they’d still consider you for the other if they thought it was a good match. Others wouldn’t. There’s just no one answer that works all the time for this scenario, so you’re left doing what feels like the most sensible option to you in the specific context you’re facing.

In this case, I do think that if you apply to the project manager position and not the senior role, they probably won’t consider you for the senior one … because you’d sort of be saying “I don’t think I’m ready for that role,” and if you don’t think you’re ready, they won’t either. Of course, the flip side of that is that if you only apply for the senior role and not the project manager role, you risk them assuming you wouldn’t be interested in the latter and thus considering you for neither.

So there’s just no perfect answer.

But given the specifics of your case, I don’t see why you can’t just apply for both. You’d need to write a separate cover letter for each (making each quite distinct from the other; no sending a generic letter here and just changing the first paragraph), and mention in each that you’re also applying for the other role and why. That feels straightforward and reasonable to me — and if it does to you too, then I say go for it; after all, part of the hiring process is to weed out people who define “reasonable” differently than you do.

{ 17 comments… read them below }

  1. Wren*

    maybe the listserve person she contacted before can provide insight into how applying to two jobs would be seen in the company culture.

  2. HR Chick*

    I applied for a manager role and was also informed about an analyst role in the same group that they were hiring for. The manager one I met the minimum qualifications for, while the analyst I was spot on, if not a little higher. They considered me for both and I ended up with the analyst role. Knowing the culture of the organization now (I’ve been here a little over a year), I’m so happy with that move that wasn’t as big of a stretch role. It’s not out of reach in the not too distant future and the company is great about shuffling around people to different assignments.

    I’d learn a little more about the organization’s culture as well — I had heard that they are good about moving people all around the organization from several people before taking the role so it wasn’t just them giving me lip service. My old company, the paths were VERY linear. If I made this move at old company, I would have regretted it. But today making that move with new company, I’m very happy with my decision.

    Good luck!

    1. Betty Jane*

      The manager role must have also been filled, but you think you will have that in the “not to distant future?” It’s great to be promoted within a company but not to expect it as it was just filled.

  3. Steve G*

    From my experience, I wouldn’t apply for the PM job unless that is a job you’d want and/or the job content is very similar to the job you’d want. 2 reasons I say this: 1) In my 2 jobs since the great recession began, I’ve seen a slow down in transitions, promotions, etc. so the transition may take longer than you’d like, and 2) something I’ve also seen is this, a persons starts to get their foot in the door, the job they take is more complicated than they anticipated, and they do good at it, but not stellar. Then they get cast-type as the “person that does xyz great, but not stellar” and no one even thinks about them for a promotion/transition/raise until they do that work they weren’t even passionate about better.

    A person I work closely with is going through #2, and it gets pretty painful for him, every single day not being able to spread his wings and do more for this or that silly reason.

    And a separate item: #3 – are you 100% sure the job is above your head? My first job out of school was an ESL teacher in Europe. I developed curricula and training for corporate clients as well, and faced every single challenge and criticism you can think about. I also run trainings/meetings in my current job as needed. Yes, its hard to be given a blank slate to write a course/training to fill x # of hours per week with no guidance, but it really is not impossible. If you’d never done training before, then you might not be qualified to begin with. But if you have, and the jump is that now you have to develop curricula from scratch, I wouldn’t consider that a huge jump out of your league. Good luck!

  4. Just a Reader*

    I applied for a management role and was redirected to a high-level individual contributor role that hadn’t been posted yet. I ended up with that job and it has been an amazing career move.

    Don’t be afraid to stretch and still strive to blow them away. If they like what you have to say but aren’t sure about the fit, they’ll talk to you about it.

  5. just laura*

    “Is this a YOLO/Lean In moment where I should apply to the harder reach of a job, or should I Lean Sideways-Diagonally-In…”

    I love this. :)

      1. Blue Dog*

        Yeah, me too. I was going to say if this is how you present, you aren’t ready for the more advanced position.

        1. Ask a Manager* Post author

          Wait, what? This is a casual letter to a blog (a blog that itself has a pretty casual tone). People often talk differently in work contexts than they do in others.

          I mean, I say stuff like “your manager is an ass” here all the time. I obviously don’t say at work (at least not in a formal context).

        2. Wakeen's Teapots Ltd*

          It’s funny.

          You wouldn’t have a dog avatar as your Linked In picture. You have one here because this is a relaxed environment where you can be funny or whimsical without worrying about what people think.

          Which, I think, cute dog.

      2. Blue Dog*

        By way of example, we had a young 2 year lawyer assign out a project on a case that had been dismissed 2 weeks before. The assigning lawyer had been the one that did the paperwork and wrote the client. 20 hours or so were spent on the new project. When the error was discovered, his response was, “Oops. My bad.” I think the response was worse than the mistake — it showed a lack maturity and judgment that spoke volumes.

      3. Sunflower*

        I read it as she wasn’t serious. Could be wrong but I would hope the majority of the professional workforce knows ‘YOLO’ is not a term you would use seriously.

  6. Joey*

    Apply for both. No manager in their right mind would turn you down if you were the best fit for either one. Just stress that the lower one and it won’t be a disappointment. Because that’s really the only concern any rational manager will have- that you really want something at the higher level, but will TAKE something the lower level in the interim. I would say the higher level position is ultimately your goal, but the bigger priority is getting into that specific company because blah blah blah. And because of that you would accept the lower level position even if someone else offered you a higher one. Boom.

  7. Mike B. (@epenthesis)*

    How desperate are you for a job, OP?

    If you’re unemployed and very nervous, then it’s probably prudent to take the safer bet. But I don’t get that impression from your letter. It sounds to me like the stretch job is a rare opportunity, while the safe job is something that will come along again soon enough. If that’s the case, go for the bigger job and don’t concern yourself too much about the safe one (unless they bring it up).

  8. Career path?*

    In my experience, training jobs are quite different (in terms of skills, work tasks etc) from project managers. This is different than applying to two jobs which are on the same career path but at different seniority levels.

    You should be able to explain to the company why you are suited for both jobs. Otherwise, you run the risk of it looking like you don’t know what you want, and that you are applying for everything.

  9. KH*

    Sometimes it is very hard to gauge jobs from the descriptions on a job board. I think you can safely tell the recruiter / HR manager that both jobs interest you and you think that you are qualified to do either.
    At the same time, remember that there is probably a candidate who is already qualified and suited for the role that you consider a stretch. So it will require a great degree of passion and cross-selling to convince them that you are the best candidate. And I think the fact that you are willing to take that risk would say a lot about your character.

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